


Shameless

by TheseusInTheMaze



Category: Game Grumps, jacksepticeye
Genre: Accident, Autofellatio, Bathroom Restriction, Crossdressing, D/s, Diapers, Domme, F/M, Humiliation, Infantilism, Mommy play, Panties, Pants wetting, Puppy Play, Vomit, Watersports, choking on cock, pants messing
Language: English
Status: Completed
Published: 2017-02-12
Updated: 2017-02-12
Packaged: 2018-09-23 18:01:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,109
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9669947
Author URL: https://archiveofourown.org/users/TheseusInTheMaze/pseuds/TheseusInTheMaze
Summary: Holly is doing her utmost best to humiliate Jack. Nothing seems to work, and things... escalate.





	

**Author's Note:**

> This fic is really, really gross. It has vomit. It has pee. It has poop. If any of that grosses you out, please move on.

“Is it physically possible to embarrass you?” Holly looked over at Jack, who had just belched so loud the whole restaurant had turned around to stare at him. He gave a few cheery waves, then went back to his sandwich.

“Probably not,” Jack said cheerfully, and he grinned. “Why? Is that a challenge?”

“I dunno,” said Holly. “Do you want it to be?”

Jack’s face took on a thoughtful cast. 

“Can I get back to ya on it?” 

“Sure,” said Holly. “But don’t do that again.”

“Or what?”

“Or I’ll tie your dick to your toe and make you go jogging.”

Jack shivered. 

“I love it when you’re mean, commander,” he told her, and he gave her a loud, wet kiss on the temple. 

Holly snorted, and she took a bite of her own sandwich. 

* * * 

“I want to try it,” said Jack, plopping down next to Holly on the couch. 

They were both at the space, waiting for a room to clear up so they could record an episode. 

“Try what?” 

“That thing we were talking about. You embarrassing me.”

“What do you want?” 

“Well,” said Jack, leaning back into the couch with his hands behind his head, “don’t shit on me. Nothing that the fans would know.”

“Fair,” said Holly. “But.. anything else is up for grabs?”

“Anything,” said Jack, with a rakish grin. 

“Well,” said Holly, her mind racing. “Starting now?”

“Yeah,” said Jack.

“Well,” said Holly, and she smiled at him with too many teeth, “how about we start now.”

Jack licked his lips, his eyes going dark. 

She licked her own lips, her arousal beginning to pool in her belly. 

“Be a good boy,” she said, leaning in to whisper in his ear, “and go into the bathroom. Take your underwear off, put your jeans back on, and bring me your underwear.”

“B-bring you my underwear?” Jack blushed a bit, then grinned. “One pair of slightly used boxer briefs, comin’ right up!”

Holly snorted, going back to her phone. 

Jack came back, not even five minutes later, and he pressed his underwear right into his pants. 

“So now what?” 

“Now,” said Holly, and she wrapped her arm around him, pulling him closer so that she could whisper in his ear, “now I want you to think about that one time when I sat in your lap and rode your cock while slapping your face.”

Jack was turning pink, but he nodded. 

When Holly looked down there was indeed a lump in his pants. 

She glanced around, but nobody was watching them. With a smirk, she grabbed him between the legs, and she squeezed his cock through his jeans.

Jack moaned, humping against her hand. 

“Jack,” Arin called from the next room, and Holly’s hand was gone from his cock. “Ready?”

“He’s ready,” Holly said, and she slapped Jack on the ass on his way to the other room.

Jack gave her a Look. 

Holly smiled. 

* * * 

Halfway through Jack’s session, Holly’s phone dinged. 

It was a picture of Jack’s sore, raw, hard cock, pulled out as Arin went to a bathroom. 

_Gonna kiss it better?_

_No, you will._

He sent her back a confused selfie. 

Holly grinned. 

* * * 

“Oh, fuck, Holly,” Jack was moaning, squirming on the bed, humping the air, Holly’s fingers buried inside of his ass.

“You like that, huh?” Holly was panting as well, her fingers twisting inside of him, jamming against his prostate. “How’s your poor dick feeling?”

“Pretty damn sore,” said Jack. “It needs all the kisses it can get, I think!”

“Well,” Holly said, “you’d best get to it, then!” 

Jack was on his back, and Holly helped him lift his legs up, then pushed them down, so that his feet were flat on the bed, holding onto one of his calves. His cock was pressed against his lower lip, and he opened his mouth, taking it in.

“Just like that,” Holly cooed, two fingers inside of him and curling, and he was hot and clenching around her, beginning to hump into her mouth. 

“Fuck,” Jack mumbled, and he took more of it into his mouth, until it was about halfway in. His back was curved at a very appealing angle, and his ass was beginning to really clench around her fingers, as she fucked him, tapping on his prostate like a telegram. 

Holly kept fucking him, watching his face, as he just… fucked his own face, which was odd. 

He was panting, whimpering around his own cock, his hips working furiously, and it was just so… cute, she couldn’t get enough of it.

“We’re totally doing this again,” Holly told Jack, curling and uncurling her fingers as she thrust. 

“I’m… fuck, Holly...,.” Jack’s cock was smeared against his cheek, no doubt catching on his scruff. “I’m gonna cum!”

“Do it,” Holly said, guiding his cock back into his mouth. “Do it, cum into your mouth, you dirty thing, fucking… oh!”

She never got tired of his face when he came, and the look of shock on his face as he came in his mouth was… fucking amazing. She needed to see that, much more often. Much, _much_ more often. 

Holly let go of his leg and removed her fingers, and Jack unbent, lying flat on his back and panting at the ceiling. 

“So do you feel humiliated?” Holly kissed his nose, which was sticky with cum. 

Ew. 

“Nope,” said Jack. “Just kinda… sore.” He grinned, then made a face. “Also, I need to eat more pineapple.”

Holly laughed. 

* * * 

“So going commando isn’t doing it,’ said Holly, the next day. “Hmm….”

“Hmmm?” Jack lay on his side, rubbing her belly lightly. His face was sticky with her arousal, and there were a few of her pubic hairs stuck to his chin. 

“Going commando didn’t bother you,” said Holly, moving up to pet his hair. It was sweaty .

“‘Course not. Why would it?”

“I dunno. Knowing if you got too excited you’d make a stain in your pants?”

“I’ve got the self control of one of those British guards,” said Jack, and he flexed.

Holly snorted and prodded him.

“Well,” she said, “I guess I’ll have to up the ante, huh?”

“Up the ante? What’re you gonna do, put me in a nappy?” 

“... maybe,” said Holly, and she filed that away for the future. “But not today.”

“What’s it today?”

“You’re gonna wear _my_ underwear,” said Holly, and she was smiling widely.

“Ooh, neat,” said Jack. He didn’t look perturbed at all! 

“And my shirt,” said Holly. 

“You have nice shirts,” Jack agreed.

Holly covered her face with both hands and groaned. 

“What embarrasses you?!” 

“Why would wearing your clothes embarrass me?” Jack sounded genuinely confused. 

“Because… actually… I’m not sure,” said Holly. “I dunno. A lot of dudes feel weird wearing women’s clothing.”

“What if i made you wear one of my skirts, too?”

“What, to work?” 

“Sure,” said Jack. “You’ve got good taste.” He shrugged. “I mean, it’s not like I’m worried about getting being beaten up or anything - I’m not going out today, except to the office.”

“Well… wear my skirt,” said Holly. “And my shirt, and my underwear.”

“Do you want me to wear your stockings too?”

“They wouldn’t fit you,” said Holly. “Your feet are just so freaking… huge!”

“You know what they say about big feet,” Jack said, and he was smirking. 

Holly snorted, and she grabbed his penis. 

“What, this little thing?” She wrapped her fingers around his cock, and she squeezed it. 

It was still sensitive from cumming, and he whimpered, squirming. 

“Does that humiliate you? If I tell you that you’ve got a tiny cock? What if I locked it up?”

“If you lock my cock up,” Jack told her, “I will get a pair of lock picks.”

“Would it humiliate you?”

“Nah. It’d just annoy me.”

“Fair enough,” said Holly. She grabbed his thigh and squeezed it. “Go get dressed, Jack.” 

“Yes, commander.”

* * * 

“So for some reason, Jack is wearing a skirt -”

“I like givin’ my balls a nice airing out now and then, thank you very much!” 

“... thanks for that, Jack.” 

* * * 

“We’re gonna try something new,” said Holly, a few days later.

She’d kept him in her underwear, because it… well, it suited him. It very much suited him. 

Maybe she needed to get him his own panties. 

She’d been stealing _his_ underwear, because goddamn, that was _really_ comfortable! 

But now… well, time to try something new.

* * * 

“What are you doing on the couch?” Holly glared at Jack. 

It was evening, and he’d just come home and kicked his shoes off. 

“Hm?”

“Dogs don’t go on the furniture without permission,” said Holly, and she held up what was in her hands. 

A doggy collar, and a special butt plug she’d bought months ago. It had a black silicone tail attached to it. 

“Oh!” Jack’s whole face lit up. 

He’d mentioned an interest in puppy play, but they’d never actually gotten around to it, what with one thing and another.

“You gonna be a good boy for me, puppy?” Holly pointed to the floor in front of her, and Jack stood up. 

Holly snapped her fingers, and gave him a Look. 

He returned it with a saucy grin, and he got on all fours, crawling up to her and whining in the back of his throat.

“There’s my good puppy,” Holly cooed, and she crouched in front of him, fastening the collar around his neck. “Now… puppies don’t wear clothes, do they?” 

* * * 

Jack sat naked on the kitchen floor, and he stared up at her with his big blue eyes. All he had was the curly puppy tail, and the collar around his neck. 

She had placed a dog dish in front of him, and told him to stay, and he was… behaving, which was unexpected. 

“We’re gonna get you your dinner, puppy,” Holly said, chipper, and she opened up the can and dumped the food into his bowl. 

Jack looked from the bowl to the can, and he whined, shifting. He opened his mouth to say something, until Holly showed him the can. 

It was chilli. Thick, chunky chilli. 

Jack leaned down, and began to eat it, surprisingly delicate. 

Holly sat down to eat her own dinner, a plate of pasta, and she fiddled with her phone.

Until she felt a tongue between her toes. 

“Jack!” Holly yelped, scandalized, and he grinned up at her. 

His face was a mess of chili, and she chuckled, leaning down to wipe it off.

He used the opportunity to lick her face, and Holly squealed, shoving at him. 

“Bad dog! Your breath stinks!”

Jack didn’t look the least repentant. He pressed his nose under her skirt, and he nuzzled up her thigh, panting with his tongue lolling out. He was mounting her leg, his cock sticky against her shin. 

“Bad dog,” Holly scolded, and she shoved him. 

He planted his knees, and nosed at her clit through her panties. 

She sighed, relaxing back into the chair as he began to lick. 

He came before she did, cum dripping down her shin, to puddle across the top of her foot. 

When he came up for air, from under her skirt, he was grinning, licking his chops.

“You didn’t even have to use any peanut butter,” he said, and he was smirking.

Holly groaned. 

“So you’re not embarrassed to have humped my leg like a dog, or eating off the floor?”

“When I’m crawling around on the floor, I am, quite literally, the perfect height for cunnilingus,” Jack told her. 

Holly snorted, and she ruffled his hair. 

“We’ll find it yet,” she told him. 

Jack licked her hand. 

“Ew!”

He was still cackling when she wiped it off on his hair. 

* * * 

“What’s that?” Jack indicated the bag on the bed.

“This?” Holly patted the bed for him to sit down. “Why don’t you, uh….” She licked her lips, and she was blushing. “Why don’t you come over here and find out?”

He padded over, his bare feet muffled by the carpet, and he sat next to her. 

“So what’s all this?” He reached for the bag, and then he blushed, before grinning at her, his eyes bright. 

“I got them at the medical supply store,” said Holly. “I mean… some of it. Not all of it.”

“Where did you get the other stuff?” Jack took out one of the packets, holding it in his hand. 

“Oh, just the drug store,” said Holly. She grinned. “Shall we… get you ready?” 

“Sounds good,” said Jack, and he looked shy, but pleased. 

* * * 

It was… surprisingly, not that weird, laying him out on the diaper, powdering him up, taping him in. 

He was adorable, with his legs forced open like that, she could just make out the lump in the diaper where his cock was pressing on it. 

She’d done her research - she had wanted to make sure she did it right, after all - so she had made sure to poke his cock down. 

His surprisingly hard cock.

Just how much was he into this? 

He smiled at her, with the pacifier in his mouth, and he reached out for her. 

“Momma?” 

“Hi,” Holly said, in her best birb voice. She leaned down to kiss his tummy, pushing his shirt up, and he squealed and wriggled under her. 

“Hi,” Jack said, and his pacifier fell out of his mouth, onto the bed. 

“What do you want, baby?” She squeezed his cock through the diaper, and he humped against her hand. 

“I want you, momma,” Jack said in his sweetest voice. 

“What else do you want, baby?” 

“Anything momma wants,” Jack said, and he held on to her shirt and cuddled up to her.

This was… unexpected, but it was nice. Quiet. 

He rested his head on her chest, and he sucked his thumb, and they savored the quiet moment. 

* * * 

“So was that embarrassing?” 

Holly gave Jack a pair of pajama pants to pull over the bulky diaper - he didn’t seem to want to take it off just yet, and he did look cute, waddling around like that. He’d nursed from a bottle, and then he’d just fallen asleep, clutching her shirt. He’d woken up in a different frame of mind, and, well… here they were. 

“Nope,” said Jack, and he looked sheepish. “I’m a bit… well, I dunno, it was so _nice_ \- I wasn’t expecting it to be so nice. You know?”

“Yeah,” said Holly. “Although I noticed you keep the diaper on.”

“Well,” said Jack, and now he was blushing. “What’s the point of wearing it, if I’m not gonna use it? Don’t wanna waste it.”

“Fair enough,” said Holly. “So you’ll be waddling the rest of the evening, huh?”

“...nope,” said Jack, and he chuckled, self conscious. “I, uh… unless I put on another one.”

“Did you just pee while you were talking to me?!” Holly pushed the waist of his pajama pants down, looking down at the diaper, and indeed, the yellow stripe had turned green. “Oh my god, Jack.” She started laughing, and he joined in. 

“So maybe I’ve thought about it a little bit,” said Jack, his cheeks pink.

“But do you feel humiliated?”

“Nah,” said Jack. “Just squishy.”

Holly wrinkled her nose.

“... can I have a new one, please?” He licked his lips. 

“... no,” said Holly, and she smirked. “And… and you’re not allowed to use the bathroom. Until I tell you to.” 

“What, I can’t poo either?” 

“... do you want me to control that?”

“I mean...,.” Jack’s expression got introspective. “I wouldn’t be… against it?”

“Another night?”

“Okay,” said Jack. “But can I get out of this wet nappy?” 

“Sure, sure,” said Holly, pulling his pants all the way down. “Baby,” she added, making eye contact.

He blushed, biting his lip, and his cock twitched in the diaper. 

* * * 

“Holly?” Jack stood in the kitchen, and he was dancing from foot to foot, pressing his legs together. He was still in his pajama pants, his butt now a lot less puffy. “Holly, I gotta go.”

Holly had been feeding him glass after glass of water - she’d given him a full baby bottle the past few times, and he’d just taken then and grinned. 

She hadn’t let him onto any carpet, though, or any soft furnishings. 

So now he was dancing in the middle of her kitchen, grabbing between his legs. 

“Let go,” she told him. 

“Holly,” Jack said, “I really… I really need to go.”

“Beg me,” she said. 

“Please let me go,” Jack said in a monotone. 

“With more feeling than _that_ ,” Holly said, making a face.

Jack snorted, and then he kept eye contact with her. He crossed his arms across his chest, and he widened his stance. 

Holly’s eyes were on his crotch, as the fabric by the head of his penis got darker, than began to drip, down his leg.

“You’re not even embarrassed!” Holly squawked, something like offended. “I cannot believe you!”

Jack laughed, and that made him pee harder, a little puddle forming under him. 

“Oh my god,” Holly said, and she was… was she angry? She wasn’t sure. Before she was even sure what she was doing, she shoved her shorts down, and she forced him onto his butt. 

“What are you doing, commander?” Jack eyed her, as she positioned herself. 

“Bend your head forward,” said Holly, and she pushed him down lower, between her legs.

She closed her eyes, and she tried to relax and think about water. 

She shivered when she felt the right valves open up, and then she was pissing, across the back of his head, dripping across the top, as she finally let go all of those cups of coffee and tea. 

“Oh my god,” Jack said, and Holly’s heart dropped.

Shit. She hadn’t asked. She’d just… done. 

“Jack, I am so sorry,” she said, and she pulled back, still peeing, making her own puddle on the floor. 

Oh, fuck, she’d… she’d ruined everything. 

“Can you do it on my face next time?” Jack stared up at her, enraptured, “Holy fuck, _Holly_!” 

“I’m sorry for not asking you,” said Holly. “I shouldn’t have done that.”

“Apology accepted,” Jack said. “You, uh… you got any more in the tank?”

“... still not humiliated?”

“Are you fuckin’ kidding me?! My totally hot girlfriend just peed on me! How much sexier can it get?!”

Holly made to ruffle his hair, then caught herself at the last moment. 

“... how are we going to make it to the bathroom?”

“I’d recommend being naked,” said Jack. “We can put the wet clothes in a bag and dump them in the laundry.”

“You’ve put a lot of thought into this, huh?” 

Jack grinned at her, cheeky. 

Holly rolled her eyes, but she grinned back. 

* * * 

“Jack, what happened to your hair? You’re gonna need to dye it again!”

Holly, sitting nearby, blushed all the way to her shoulderblades, and kept typing. 

Jack just grinned at Suzy.

“Used the wrong kind of shampoo,” he told her. 

* * * 

“So. Um.” Holly was embarrassed. Well on her way to being humiliated. How about that?

“Um?” Jack teased her. 

“How would you feel about sucking cock again? Sucking one of my cocks, I mean?”

“Sure,” said Jack. “Sounds like fun!” 

“And… what if I.. total bathroom control. And maybe making you… lose control of… other stuff.” 

“Yeah?” Jack licked his lips. “I’d be… willing to try, if you elaborated.”

She elaborated.

He blushed, but he nodded. 

“I wanna see if I am well and truly shameless,” he said. 

“Fair enough,” said Holly. 

* * * 

She started to prepare on Friday. 

“Here you go,” she said, and she put a big bowl of oatmeal in front of him. 

Jack raised an eyebrow. 

“I put flax seed in it,” she said. “And raisins. And almonds.” 

“Let me guess,” Jack said. “There will be prunes in my future.”

“Yep,” Holly said cheerfully. 

“Great,” Jack said, unenthusiastic. 

Holly smiled at him, and he managed a grin back. 

* * * 

“Um,” said Jack, and he looked genuinely uncomfortable, for the first time. 

He was standing in the middle of the living room, shifting from foot to foot. 

He was on hardwood, thankfully - he was, once again, banned from soft furnishings and carpeting. 

It was Saturday, in the middle of the day. 

And Jack was shifting from foot to foot, looking genuinely uncomfortable. 

“Um?” Holly stood up, and she was walking a little funny herself - she wasn’t used to the particular… attachment, tucked into her shorts. 

“I….” Jack licked his lips. “I need to….”

“Yeah?” She kept her eyes on his face. 

“Do you want me to do it… right here?”

There was a garbage bag by the couch. They had prepared. 

Kind of.

“Yeah,” said Holly, and she blushed. 

“... I dunno if I can do it if you’re staring at me.”

“Well,” said Holly, “I, uh… that’s too bad. Because… because I want to see your face.”

Jack gave a heavy sigh, and he screwed his face up and grunted. His cheeks turned red. 

Holly grabbed his hands, and she stared at him, enraptured - he was… well, he was about this close to crying, and he kept stealing glances at her. He’d lost his cockiness, and looked genuinely embarrassed. 

Then he sighed, and he shivered. 

“I.. I’m… I did it,” he said, quiet. 

He brightened up a bit, and those tantalizing bits of humiliation were gone. 

“That wasn’t so bad!” 

“On your knees,” Holly said. 

Jack’s face flushed a deeper red. 

“But - “

“I don’t care,” Holly said, and her voice was shaky. “Get… get down. Sit on the floor.”

“But - “

“If I hear anything but “yes, commander” or your safeword, I’m going to spank you with my belt,” said Holly. 

They’d have to replace the belt, but the way he blanched made it totally worth it. 

“Yes, commander,” Jack said, and he sat down, gingerly. When his backside made contact with the ground, he pulled a truly glorious disgusted face. 

“Good boy,” said Holly, as Jack rested his whole weight on his… no doubt squishy backside. 

Jack bit his lip, and his eyes were shiny.

“Are you… are you ready to suck my cock?” 

Jack nodded. 

Holly made eye contact with him, and she gave a thumbs up. 

He gave one back, and a shaky smile. 

He could still smile. So he wasn’t as humiliated as he wanted to be. 

Holly pulled out her rainbow strap on - her thickest one - and she pressed the tip of it against Jack’s lips. 

Jack took it into his mouth, as pretty as he sucked his own cock, and he leaned forward.

There was an… unpleasant sound, and then he was whimpering around her cock, as she pressed deeper. 

And deeper. 

He gagged when his nose was against her harness. 

She drew her cock back, then pushed it back into his mouth, and he gagged again, harder. 

The dildo was all the way in, down his throat, and he was… yeah, he was crying, clinging to her legs, and he was gagging harder. 

He threw up around her cock, and it got on her bare feet. 

Oh, that was unpleasant. That was immensely unpleasant. 

He was still throwing up, as she fucked his face, until he was tapping her hip and shaking his head. 

She pulled out, and he doubled over, gagging and vomiting, from his mouth, from his nose. There were tears dripping down his face, puddling under him, and he was sitting flat in his mess and crying. 

“I’m sorry,” Jack sobbed. “I’m sorry, I’m sorry, please don’t hate me, please, please, I’m _sorry_.” 

“Shhh,” said Holly, and she crouched down and hugged him, heedless of the puke on his shirt. She kissed his forehead and she rocked him, kissing the tears off of his cheeks. 

They were salty. 

Jack kept crying, and she kept holding him, for a solid five minutes, until her knees were sore, but she didn’t move, until he pulled back.

“Wow,” said Jack, and he smiled at her, shaky. “That was… amazing.’’

“What, crapping your pants and throwing up on me?”

“Well, okay, no, that was… really gross,” said Jack, and he laughed, a hiccuping laugh. “But, uh… the… being that vulnerable, it was… amazing.” 

Holly laughed. “You’re incorrigible,” she told him. 

He smiled, and he wiped his eyes.

Then he made a face.

“I need a shower, like… yesterday.” He wrinkled his nose. 

It was a bit… fragrant. It was a good thing they’d blocked all the cats from the room. 

“Okay,” said Holly. “Just sit tight.”

“And new jeans,”Jack called, as Holly walked gingerly towards the kitchen, to get some old dish towels.

Holly rolled her eyes.

Oh, Jack.


End file.
